Exploiting phosphonate chemistry in metal-mediated dearomatization: stereoselective construction of functionalized spirolactams from arene ruthenium complexes.

  title={Exploiting phosphonate chemistry in metal-mediated dearomatization: stereoselective construction of functionalized spirolactams from arene ruthenium complexes.},
  author={F. Christopher Pigge and John J. Coniglio and Rashmi Dalvi},
  journal={Journal of the American Chemical Society},
  volume={128 11},
Arene ruthenium complexes possessing beta-amido phosphonate side chains participate in intramolecular spirocyclization reactions to deliver stable cyclohexadienyl ruthenium adducts. Spirocyclization is accomplished via a tandem two-step sequence that involves stereoselective nucleophilic aromatic addition to the ipso position of the coordinated arene, followed by intermolecular Horner-Wadsworth-Emmons olefination. The resulting eta5-cyclohexadienyl complexes can then be diastereoselectively… 
46 Citations

Palladium-Catalyzed Tandem Reaction of Alkyne-Based Aryl Iodides and Salicyl N-Tosylhydrazones to Construct the Spiro[benzofuran-3,2′-chromene] Skeleton

A convenient palladium-catalyzed tandem reaction of aryl iodides and salicyl N-tosylhydrazones has been achieved to afford a series of compounds containing the novel spiro[benzofuran-3,2′-chromene]

Organocatalytic domino Michael/cyclization reaction: efficient synthesis of multi-functionalized tetracyclic spirooxindoles with multiple stereocenters

The asymmetric domino reaction of various 3-nitro-2H-chromene derivatives 2 to 3-isothiocyanato oxindole 3 with moderate to good enantioselectivities, employing readily available bifunctional

Metal-free spirocyclization of N-arylpropiolamides with glyoxylic acids: access to complex azaspiro-fused tricycles.

The utility of the protocol was illustrated in a one-pot reaction sequence consisting of Ugi-reaction/spirocyclization/aza-Michael transformation for the construction of complex tricyclic cores having quaternary spirocenters.

Enantioselective Annulation Reactions of Bisenolates Prepared Through Dearomatization Reactions of Aromatic and Heteroaromatic Diesters

A one-pot, enantioselective strategy for the dearomatization–annulation of aromatic diesters to give a range of highly functionalized polycyclic molecules with excellent enantioselectivity is

Squaramide-catalyzed asymmetric Michael/cyclization cascade reaction of 3-isothiocyanato oxindoles with chalcones for synthesis of pyrrolidinyl spirooxindoles

A highly efficient method for the construction of pyrrolidinyl spirooxindoles with 3-isothiocyanato oxindoles and chalcones via a Michael/cyclization cascade reaction has been developed by using

Palladium-catalyzed intramolecular ipso-Friedel-Crafts alkylation of phenols and indoles: rearomatization-assisted oxidative addition.

A novel synthetic method for spirocyclic molecules based on palladium-catalyzed intramolecular ipsoFriedel–Crafts alkylation of phenols and indoles is reported, which results in the formation of aza-spirocycles.

DFT Studies on the Palladium-Catalyzed Dearomatization Reaction between Chloromethylnaphthalene and the Cyclic Amine Morpholine

Density functional theory calculations have been performed to investigate the mechanisms of the Pd-catalyzed dearomatization reaction between chloromethylnaphthalene and the cyclic amine morpholine.